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It wasn't easy to whittle down more than 150 entries into this year's five winning cookies. This year's batch ranges from longtime friends of the Holiday Cookie Contest to bakers who developed a winning recipe right out of the gate. All belong on your cookie tray and are delicious additions to our Cookie Finder. Find these and all the other past winners at


Earl Grey Butter Cookies with Dark Chocolate-Orange Filling

Catie Fesko

Baker: Catie (Seltz Drew) Fesko of Ham Lake.

The scoop: The famous oval-shaped Pepperidge Farm cookies are a favorite of Fesko's, but she rarely sees them made in home kitchens. "I wanted to develop a grown-up version with influences of my favorite flavors — Earl Grey tea, dark chocolate and orange."

Hold the gluten: Fesko followed a gluten-free diet for eight years, and says this recipe turns out "quite well" if gluten-free flour is used in place of all-purpose flour.

First time's a charm: When she was eating gluten-free, Fesko said she became used to reconfiguring recipes to make them work for her diet. "I just got more and more confident," she said. "But I'll be honest, this is the first time I've ever developed a totally new recipe from scratch and I'm glad it was such a success."

A winning year: "This was just a fun idea I had seen advertised in the Star Tribune — I didn't expect to win," she said. She only made the winning recipe twice before being satisfied with the outcome. "It must be a fluke," she said with a laugh. But her winning ways started earlier this year; her almond cake won a red ribbon at the Minnesota State Fair in the international cake category. She had so much fun with that contest, she decided to give this one a whirl.

Baker's tip: The cookies are crisp and delicious and very Milano-like the first day, but as they sit, the cookies become softer (which isn't a bad thing). "But if you're expecting a nice, crunchy cookie, definitely try to eat them within a day or two." And Fesko's tip for using a toothpick when piping the cookies (see the recipe) is a stellar one.

A chocolate note: Fesko is a fan of dark chocolate, but you can tailor the chocolate to suit your tastes. You'll have extra dark chocolate-orange ganache, but don't let it go to waste: Form it into small truffles, heat it up and spoon it over ice cream or dip a spoonful into a mug of hot chocolate for an elevated cocoa experience.

Judges' comments: "I just want a cup of tea with this." "It did remind me of a Pepperidge Farm cookie; it had a certain nostalgia." "I like that all those flavors come through without any of them overwhelming the other." "The textures were really fantastic; the crispness of the cookie and the richness of the ganache worked really well together." "It's not hard. Of all the complicated cookies in the world, this one is not but it looks like it is." "I love that it's going to push people to do a different technique with the piping bag." "It's a good dunker."

Find the recipe here.


Ginger Chocolate Bliss

Lori Lippert

Baker: Lori Lippert of St. Paul.

The scoop: A fresh take on the classic chewy ginger molasses cookie turns it into a warmly spiced chocolate- and gingery ganache-filled sandwich.

A ginger winner: Lippert is devoted to the ginger cookie recipe from "Once Upon a Tart," which packs in cocoa and lots of warm and wintry spices. She also liked the Serious Eats recipe for a crispy lemon-ginger sandwich cookie. So, she merged the two together (minus the lemon). "Then I thought, how can I make it special? How can I make it different? And how can I make it my own?"

If at first you don't succeed: It was a retirement goal of Lippert's to enter the Star Tribune cookie contest (the other was to do a floral arrangement for Art in Bloom). She entered last year with an earlier version of this cookie, only with a cream cheese filling. When it didn't advance in the contest, she gave it another look. "I thought I'd change it up this year and try something else, and I guess that caught people's attention."

Judges' comments: "That ginger cookie on its own is great." "I'm a sucker for a little sparkle." "I like the snap of the cookie, and I like how the ginger hits you at the end." "The filling is fairly restrained but very tasty." "It's a different kind of sandwich cookie."

Baker's tips: "I always just bake one sheet at a time. Always use parchment paper. Watch them like a hawk. And have a really good recipe!"

Working ahead: Lippert makes about 10 different kinds of cookies for her "huge" family's holiday gatherings (and almost all of them are previous cookie contest winners). To keep things expedient, she makes her Ginger Chocolate Blisses ahead of time and freezes them. "And usually it's cold enough that I can put them on the porch and keep them frozen." She brings them down to room temperature just before serving.

Find the recipe here.


Good Thai Dings

Michelle Laurent and Grace Laurent
Michelle Laurent and Grace Laurent

Baker: Michelle Laurent of Chanhassen and Grace Laurent of Minneapolis.

The scoop: A treat inspired by takeout. A tender peanut butter cookie meets the flavors of Pad Thai with lime, ginger and even a savory chili-lime seasoning.

Takeout treats: Over dinner one night, Michelle Laurent was struck with an idea for a cookie unlike any other. "I had Pad Thai one night and I thought peanuts and lime and ginger are really good together and those would translate to sweet from savory. So we just started monkeying with it."

Mother-daughter project: Michelle collaborated with her daughter Grace to refine the cookie. Starting with a circa 2000 newspaper clipping of a peanut butter and honey cookie recipe from the Star Tribune, they experimented with the additional flavors over the course of several months. It was a fruitful partnership. "I came up with the original idea, but Grace was the one who really pushed — more ginger, we need more lime, we need more Tajin," Michelle said.

Spice is nice: The Laurents like a little bit of heat in their cookies, which they bring to this recipe via Tajin, a Mexican chili-lime seasoning. It's not as far-fetched as one might think. "Like a gingerbread cookie, we always put pepper in ours for a little bit of zip to it," Michelle said.

Baker's tip: Make sure you are following a recipe you trust, Laurent said. Michelle follows Dorie Greenspan, America's Test Kitchen and Sarah Kieffer for tried-and-true cookie recipes. (Kieffer's candied nuts recipe from her "100 Cookies" cookbook was the source for the Good Thai Dings topping.)

Judges' comments: "This is the one where you taste it and it surprises you."

Find the recipe here.


Aperol Sparklers

Joanne Holtmeier

Baker: Joanne Holtmeier of Edina.

The scoop: Cheers! A summery cocktail gets the holiday cookie treatment in these orange-scented shortbreads with a sparkly, peachy-pink glaze — and a hit of Aperol liqueur.

Aperitivo hour: One of Holtmeier's favorite cocktails is the Aperol Spritz, a drink made with prosecco and the sweet, slightly bitter and citrusy Italian liqueur Aperol. She first tasted it in Italy about a decade ago and was hooked. "It's very pretty and summery and an easy and beautiful drink to have before dinner," she said. By showcasing orange, she brought the cocktail from summer into winter in cookie form.

Cocktail inspo: In addition to being an avid baker, Holtmeier loves making cocktails at home. So much so that there's a common ingredient in many of entries to the Star Tribune cookie contest over the years: liquor. It's a way to clear out the liquor cabinet, she said. "It's like, oh no, I've got this leftover liqueur that I bought to make a drink and I don't need it; let's use it in some other way." She has designed previous finalists around Creme de Menthe, Irish Cream and Limoncello.

Repeat finalist: Holtmeier has been recognized in our contest more than any other entrant, winning in 2020 with her Spumoni Squares and being named a finalist five other times. She's also a ribbon winner in State Fair contests. Fitting, then, that Marjorie Johnson is her "idol." It's not that she's competitive, exactly. "I just think it's fun to try things," she said.

Judges' comments: "You do get the Aperol, and there's a little bitter in the back." "It's a bright flavor, and it's nice especially in the winter." "It feels Christmassy." "It puts you in a whole different mood." "It's like a very elegant slingback shoe."

Baker's tip: One of Holtmeier's longtime baking pet peeves was rolling logs of dough to be refrigerated before baking, and after a half-hour, "I'd pull it out and it'd be flat on the bottom." Her fix? Slitting open a tube from a roll of paper towels, and setting the log inside to keep the bottom edge round. "That to me was a game-changer."

Find the recipe here.


Nanaimo Bar Thumbprint Cookies

Annette Gustafson

Baker: Annette Gustafson of Maple Grove.

The scoop: A candy bar as a cookie. A chewy, chocolaty cookie with a creamy frosting-like center, drizzled with bonus chocolate.

A candy bar connection: "We can thank our Canadian neighbors to the north for Nanaimo bars. These delicious treats inspired my recipe," Gustafson wrote in her entry. Nanaimo bars originated in Nanaimo, British Columbia. Traditional Nanaimo bars require no baking and have three layers: a crumb base layer with graham crackers, shredded coconut, cocoa and nuts; a creamy custard buttercream filling in the middle; and a chocolate top layer. There are variations, especially with the filling. These cookies are already a winner of sorts: although she created the recipe for our contest, Gustafson entered them in the State Fair this summer and brought home a red ribbon.

Judges' comments: "It's a good, moist chocolate cookie, almost brownie-like."

Flavor booster: The center of Gustafson's cookie calls for custard powder, which isn't a common ingredient in American baking. However, attentive viewers of "The Great British Baking Show" might have caught it in an episode of the most recent season. It was invented in 1837 by British chemist Alfred Bird, whose wife was allergic to eggs (the primary ingredient in most custards). Bird's custard powder is utilized as a thickening agent for a creamy, eggless consistency.

Baker's tip: Find Bird's custard powder at World Market or other local specialty shops that import ingredients from the United Kingdom. But don't worry if you can't find it — vanilla pudding mix works, too. And here's one more tip from our baking pros. How do you make a thumbprint cookie look good without using your thumb? Use the handle of a wooden spoon, before and after baking.

Previous entry: Gustafson's baklava cookies were notable submissions in last year's cookie contest. The skill required made it a fun baking project for more experienced bakers, and the results were a tasty contender.

Find the recipe here.